Abstract Over 72 exploration wells have been drilled on the Caribbean islands of Hispaniola and Puerto Rico over the past century, but with no commercial success. A question is whether these Caribbean oceanic islands have experienced sufficient subsidence and burial for any potential source rocks to reach maturity and produce commercial hydrocarbons. Subsurface data from previous studies were compiled into a regional depth to basement and sediment thickness map for Hispaniola, Puerto Rico and their offshore areas. The thickest basins include the Enriquillo/Cul-de-Sac basin (6.3 km), San Juan/Plateau Central basin (5 km), Azua basin (2.8 km), Cibao basin (5 km), North Coast basin (2.5 km), South Coast basin (1.3 km), Haiti sub-basin (3.7 km), Hispaniola basin (3.5 km) and San Pedro basin (3 km). One-dimensional modelling for six onland basins shows that only the Azua basin of the south-central Dominican Republic has reached sufficient maturity to place potential source rocks into the oil window. Our study shows that commercial hydrocarbons are possible in the deeper basins – Azua basin, San Juan–Plateau Central basin and Cibao basin of Hispaniola – but unlikely in the shallower basins that lack sufficient overburden for organic maturity.